About Olly Olly
Olly Olly is a $25M ARR digital marketing company with 350 employees helping small, local businesses grow without becoming marketers. We're transitioning from a website-plus-marketing-tools platform into an intelligent growth operating system—built on the philosophy that marketing should be automatic, not accidental.
Our customers are busy contractors and professional service providers drowning in 5-7 fragmented marketing vendors. They don't want to learn local SEO or manage review workflows—they want to focus on their craft while their online presence "just works." We solve the fragmentation trap with software that systematizes our services team's expertise and automation that removes marketing decisions from business owners' plates entirely.
Role Overview
We're hiring a Head of Product to architect the future state of Olly Olly while maintaining current customer value. This is a transformation year—not iterating a mature product, but building our 2026 vision of an automation-first growth OS.
You'll own end-to-end product strategy and execution, leading a team of 1 (Product Manager) with 80% strategic / 20% tactical focus. You'll co-create product vision with the CEO, run outcome-driven cross-functional partnerships with Design, Engineering, Revenue, and Marketing, and build a high-impact product that drives activation, retention, NPS, and revenue lift.
The Challenge:
Today: Make local SEO and online visibility automatic for people who hate marketing.
Tomorrow: Design systems sophisticated enough to demo Olly Auto's power, yet obvious enough that a plumber can onboard self-serve. Make running a local service business automatic for people who want to focus on their craft, not operations—from first customer touchpoint through final invoice and review follow-up.
Your role: Architect the bridge from where we are to where we're going, while maintaining current customer value throughout the transformation.
What You'll Own
Product vision & roadmap across our growth OS:
- Product vision & roadmap across our business operating system: AI-driven automation (Olly Auto), smart scheduling, invoicing/estimates, customer communication workflows, revenue optimization tools, and local visibility infrastructure—everything between 'lead comes in' and 'customer refers you.
- "Below the waterline" systems: citation building, directory management, GBP Guardian/protection, review workflows—the 90% invisible work that makes marketing "just work"
- New product bets: AI-generated business audit reports (lead gen), invoice/estimate tools, waitlists, free trial infrastructure, competitive moats against Angi and traditional agencies
Services-to-software transformation:
- Productize what our 350-person services team does manually; build tools that scale their expertise
- Partner with Operations on services-to-software roadmap; understand which manual processes should stay human-touch vs. which create product opportunities
- Design the interplay between human-delivered and automated work so Creative and SEO specialists focus on high-value strategy, not repetitive execution
Strategy to outcomes:
- Set clear goals tied to activation, retention, NPS, and revenue; run an outcome-driven product operating rhythm
- Prove key product bets: Can we automate GBP management to the point customers never think about it? Will AI audit reports drive qualified pipeline? Can scheduling/invoicing deepen engagement and prevent churn?
- How do we design automation that makes small business owners 10x more productive—handling more customers with fewer people and less time spent on operations?
Customer research & insights:
- Stand up a disciplined research practice with CS, Support, and Data; master our ICP (the contractor who wants marketing to "just work")
- Translate insights into sharp product bets that solve the fragmentation trap
Dual GTM motion:
- Design for sales-led demos AND self-serve PLG; partner with Sales on proof points, packaging, and feedback loops
- Collaborate with RevOps, Sales, and Marketing on pricing, tiers, paywalls, and conversion funnels
Product execution & delivery:
- Lead cross-functional pods to scope, validate, build, and launch; balance speed with polish
- Champion elegant, obvious flows; translate complex backend systems (APIs, integrations, AI logic) into effortless UX
Data-driven decisions:
- Instrument the product (e.g., Mixpanel) and build a metrics culture; make calls with qualitative + quantitative proof
Technical partnership:
- Collaborate with Engineering on trade-offs, integrations, and architecture without compromising UX
Team leadership:
- Manage and grow Product; coach for clarity, autonomy, and accountability
Cross-functional influence:
- Co-create strategy with founders/executives on positioning and product-market fit
- Co-own website and content workflows with Product Marketing/Design; coordinate with Marketing on external comms to ensure message-product fit
Core Competencies
- Full-stack product ownership: Strategy → execution across SaaS + services; deep product knowledge with founder-level collaboration on vision
- SMB + automation mastery: Built tools for small business operators who need simplicity and power; understand how to remove decisions, not add features. Ideally across workflow automation, scheduling, invoicing, CRM, or business management platforms—not just marketing tools"
- AI-forward: Comfortable using and shipping AI features responsibly; embrace value-add automation use cases
- Services mindset: Know how to systematize human expertise into scalable software; design the human-automation handoff
- Technical empathy: Strong Engineering partner; speak API/integration/architecture fluently enough to make smart trade-offs
- Research to roadmap: Turn customer insight and ICP mastery into ruthless prioritization and clear specs
- Design sensibility: High bar for usability; sweat interaction details where it matters; make complexity feel simple
- Dual GTM fluency: Thrive in sales-led + PLG hybrid; design for demos and self-serve simultaneously
- Builder's grit: Startup mentality, bias to action, sleeves-rolled, hands-on when needed; appetite for ambiguity in transformation year
Qualifications
Must-haves:
- 7–10+ years in Product Management, including 5+ years in product leadership (manager or head-of-function)
- Proven success shipping high-impact SaaS products for SMBs, ideally in workflow platforms, scheduling tools, marketing enablement, or service business operations
- Demonstrated success building AI-enabled user experiences and automation-first products
- Strong analytics chops and product instrumentation (e.g., Mixpanel, Jira); comfort defining and owning KPIs
- Excellent written specs, storytelling, and stakeholder management across Execs, Sales, CS, Engineering, and Design
- Based in or relocating to Austin, TX; embrace hybrid cadence with regular in-office collaboration
Nice-to-haves:
- Experience co-owning pricing/packaging with RevOps for a sales-led org
- Background in local SEO, reviews/reputation, or lead-gen workflows for service businesses
- Prior success building small, senior-leaning product teams from 0→1 or 1→N
- Experience productizing services or designing human-automation workflows
- Experience with business operations platforms (invoicing, scheduling, CRM) or vertical SaaS for service businesses
Why Choose Us
Join us during this pivotal transition as we transform from an agency to a human-centric SaaS provider. Your ideas, strategies, and solutions will directly impact the success of small businesses—and our own growth.
You’ll have the autonomy to build from scratch, the support of seasoned leaders, and the chance to see your work shape the next era of Olly Olly’s story.
Let’s shape the future of small-business growth together.
Diversity and Inclusion at Olly Olly
At Olly Olly, we celebrate differences in background, culture, abilities, and perspectives—because diversity drives innovation and creativity. Your voice matters here, and your unique perspective will help us shape the future of small-business growth.
